Synthesis of enantiomerically enriched Baylis–Hillman alcohols from their acetates: combination of kinetic resolution during the salt formation with (DHQD) 2PHAL and following asymmetric induction during hydrolysis with NaHCO 3 as a water surrogate

Abstract

Enantiomerically enriched Baylis–Hillman alcohols 2a– d ( S) were prepared in 25–42% yields with optical purities of 54–92% ee by using the combined concept of kinetic resolution during the salt formation of racemic Baylis–Hillman acetates 1a– d with (DHQD) 2PHAL and the asymmetric induction during the S N2′ type reaction with sodium bicarbonate as a water surrogate.